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162353

Sigma-Aldrich

3-Methyl-2-buten-1-ol

99%

Synonym(s):

3,3-Dimethylallyl alcohol, Prenol

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About This Item

Linear Formula:
(CH3)2C=CHCH2OH
CAS Number:
556-82-1
Molecular Weight:
86.13
Beilstein/REAXYS Number:
1633479
EC Number:
209-141-4
MDL number:
MFCD00002916
UNSPSC Code:
12352100
eCl@ss:
39020334
PubChem Substance ID:
24849980
NACRES:
NA.22

vapor pressure

1.4 mmHg ( 20 °C)

Quality Level

100

assay

99%

form

liquid

expl. lim.

16.3 %

refractive index

n20/D 1.443 (lit.)

bp

140 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

functional group

hydroxyl

SMILES string

C\C(C)=C\CO

InChI

1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

InChI key

ASUAYTHWZCLXAN-UHFFFAOYSA-N

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General description

3-Methyl-2-buten-1-ol reacts with nitrosocarbonyl benzene to yield 5-hydroxy-isoxazolidines. It is commonly used as fragrance ingredient.

Application

3-Methyl-2-buten-1-ol was used as starting reagent during asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone via Sharpless asymmetric epoxidation reaction.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

124.7 °F - closed cup

flash_point_c

51.5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0844
STBJ9976
STBJ9204
10524KC
06311KC069

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Hong Liang et al.
Metabolic engineering, 65, 223-231 (2020-11-29)
Engineering microbes to utilize non-conventional substrates could create short and efficient pathways to convert substrate into product. In this study, we designed and constructed a two-step heterologous ethanol utilization pathway (EUP) in Escherichia coli by using acetaldehyde dehydrogenase (encoded by
Anastasia Zerva et al.
Molecules (Basel, Switzerland), 23(9) (2018-09-22)
Feruloyl esterases (FAEs, E.C. 3.1.1.73) are biotechnologically important enzymes with several applications in ferulic acid production from biomass, but also in synthesis of hydroxycinnamic acid derivatives. The use of such biocatalysts in commercial processes can become feasible by their immobilization
Charla A Centrone et al.
Bioorganic & medicinal chemistry, 12(21), 5495-5503 (2004-10-07)
Mycobacteria biosynthesize a cell wall structure that is rich in polysaccharides containing arabinofuranose residues. The source of these arabinofuranose residues is decaprenolphosphoarabinose (1), the donor substrate for mycobacterial arabinosyltransferases. We have previously demonstrated that an analog of 1, C-phosphonate 7
Huawei Liu et al.
Chirality, 18(4), 223-226 (2006-03-08)
The asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone were achieved by using the Sharpless asymmetric epoxidation reaction to generate the stereogenic center and a ring-closing metathesis (RCM) for the formation of the lactone structure. Starting from 3-methyl-2-buten-1-ol, the asymmetric total
Dusan Hesek et al.
Journal of the American Chemical Society, 134(33), 13881-13888 (2012-08-07)
We describe a practical, multigram synthesis of (2Z,6Z,10Z,14Z,18E,22E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-ol [(Z(4),E(2),ω)-heptaprenol, 4] using the nerol-derived sulfone 8 as the key intermediate. Sulfone 8 is prepared by the literature route and is converted in five additional steps (18% yield from 8) to (Z(4),E(2),ω)-heptaprenol
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